GB1601983A - Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils - Google Patents
Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils Download PDFInfo
- Publication number
- GB1601983A GB1601983A GB22711/78A GB2271178A GB1601983A GB 1601983 A GB1601983 A GB 1601983A GB 22711/78 A GB22711/78 A GB 22711/78A GB 2271178 A GB2271178 A GB 2271178A GB 1601983 A GB1601983 A GB 1601983A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aqueous
- xxx
- glycol
- epoxide
- fat
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000003921 oil Substances 0.000 title claims abstract description 48
- 239000002304 perfume Substances 0.000 title claims abstract description 33
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 71
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- -1 hydroxyalkyl ether Chemical compound 0.000 abstract description 3
- 238000007046 ethoxylation reaction Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract 2
- 150000002118 epoxides Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 description 39
- 239000000243 solution Substances 0.000 description 19
- 150000001336 alkenes Chemical class 0.000 description 18
- 239000000203 mixture Substances 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 244000131522 Citrus pyriformis Species 0.000 description 2
- 240000006497 Dianthus caryophyllus Species 0.000 description 2
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000010627 cedar oil Substances 0.000 description 2
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 235000019477 peppermint oil Nutrition 0.000 description 2
- 239000010665 pine oil Substances 0.000 description 2
- 239000001738 pogostemon cablin oil Substances 0.000 description 2
- 239000010668 rosemary oil Substances 0.000 description 2
- 229940058206 rosemary oil Drugs 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 240000004760 Pimpinella anisum Species 0.000 description 1
- 235000012550 Pimpinella anisum Nutrition 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000010642 eucalyptus oil Substances 0.000 description 1
- 229940044949 eucalyptus oil Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010643 fennel seed oil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Abstract
The solution contains hydroxyalkyl ether ethoxylates, which are suitable at a low application concentration as solubilisers for a large number of different perfume oils. The solubilisers are prepared by reaction of the relatively long-chain epoxides with ethylene glycol and subsequent ethoxylation.
Description
(54) STABLE, AQUEOUS OR AQUEOUS-ALCOHOLIC SOLUTIONS
OF FAT-SOLUBLE PERFUME OILS
(71) We, HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN, a German company of 67 Henkelstrasse, 4000 Dusseldorf-Holthausen, Federal Republic of Germany do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:
The invention relates to stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils which contain hydroxyalkylether-oxethylates as dissolving intermediaries.
In many cases, water-soluble perfume oils may be used for the purpose of perfuming clear, aqueous or low percent alcoholic cosmetics such as face lotion, after-shave lotion and hair lotion. However, the majority of etheral perfumes, perfume oils and fragrances are oil-soluble products which can be converted to clear, stable aqueous or aqueous-alcoholic solutions only by the addition of so-called dissolving intermediaries. It is already known to solubilise oil-soluble products by using various dissolving intermediaries such as monofatty acid esters of polyols such as sorbitan monostearate or various ethylene oxide addition compounds such as polyoxethylated castor oil. A substantial disadvantage of the dissolving intermediaries used hitherto is that relatively large quantities have to be added in order to convert the desired and required quantities of perfume oils to a stable, aqueous or low percent alcoholic solution. A further disadvantage is that their action as a dissolving intermediary is generally very specific and extends to a limited number of perfume oils.
Therefore, the task arose of providing dissolving intermediaries which, even when added in small quantities, render it possible to convert the largest possible number of different perfume oils in the desired and required concentration to a clear, stable, aqueous or low percent alcoholic solution.
In accordance with the invention, this object is achieved by clear, stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils, characterised by a content of hydroxyalkylether-oxethylates of the general formula
in which Rl and/or R2 represent an alkyl group in 1 to 24 carbon atoms or hydrogen, preferably 12 to 18 carbon atoms, or R; and/or R4 represent an alkyl group having 2 to 22 carbon atoms or hydrogen, preferably 12 to 18 carbon atoms, with the proviso that the total of the carbon atoms of R1 + R2 or R3 + R4 lies in the range of from 2 to 26, preferably from 6 to 20, and x and y can represent integers of from 1 to 16, preferably 8 to 14, with the proviso that the total of the integers x + y has values of from 2 to 18, preferably 8 to 14.
By way of example, the hydroxyalkylether-oxethylates contained in the solutions in accordance with the invention can be produced in a two-stage synthesis by reacting longer-chain epoxides, which can be produced by known methods from olefins of various origin, with ethylene glycol in the presence of alkaline or acid catalysts and subsequent ethoxylation by known methods. Hydroxyalkylether-oxethylates of this type are described as constituents of washing agent formulations in, for example, German Offenlegungsschrift
No. 1,910,765.
End position epoxyalkanes i.e. 1,2-epoxyalkanes suitable for use as starting materials for producing the hydroxyalkylether-oxethylates are those having chain lengths in the range C12.C18. Preferred inner position epoxyalkanes acting as starting materials are derived from mono-olefins of a C11-C14 fraction and a C15-C18 fraction having the following chain length distributions: C11 -C14 fraction: C11 olefins approximately 22 percent by weight
C12 olefins approximately 30 percent by weight
C13 olefins approximately 26 percent by weight
C14 olefins approximately 22 percent by weight
C15-C18 fraction: C15 olefins approximately 16 percent by weight
C16 olefins approximately 32 percent by weight
C17 olefins approximately 43 percent by weight C18 olefins approximately 9 percent by weight
Furthermore, mixtures of unbranched and 2-alkyl-branched olefins having a content of inner position olefins, such as are produced during ethylene oligomerisation in accordance with Ziegler with subsequent peaking (Ullmann's Encyclopädie der technischen Chemie,
Vol.7, page 210, Verlag Chemie, Weinheim, 1974) may be used as a starting material for the epoxyalkanes.
A composition of an olefin fraction of this type is given, without the limiting the subject of the Application.
C16t18 fraction: C14 olefin maximum 2 percent by weight
C16 olefin approximately 50 percent by weight
C18 olefin approximately 38 percent by weight C2() olefin approximately 10 percent by weight
The composition is classified according to structures:
Unbranched, end position olefins approximately 60% 2-alkyl-branched, end position olefins approximately 25%
Inner position olefins approximately 17%.
The hydroxyalkylether-oxethylates derived from unbranched and 2-alkyl branched end position Cl4-Cl6 or C16-C18 epoxyalkanes and from inner position C15-C18 epoxyalkanes, and having 8 to 14 ethylene oxide groups added thereto, are particularly important as dissolving intermediaries in the clear, stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils in accordance with the invention.
Preferred compounds are products of reaction of a-Cl4,l6-epoxide + glycol + 9 EO, a-Cl4,16-epoxide + glycol + 10 EO, a-C14116-epoxide + glycol + 11 EO, a-C16118-epoxide + glycol + 8.7 EO, a-Cl6Xl8-epoxide + glycol + 11 EO, a-C16118-epoxide + glycol + 13 EO, i-Cls,18-epoxide + glycol + 9 EO, i-C15/18-epoxide + glycol + 10 EO, i-C15118-epoxide + glycol + 11 EO.
Suitable fat-soluble perfume oils are natural or synthetic etheral oils of all types, such as orange oil, pine oil, peppermint oil, eucalyptus oil, oil of lemons, carnation petal oil, cedar wood oil, bergamot oil, rosemary oil, patchouli oil, lavandine oil, spike oil, rose oil, vetiver oil, fennel oil, aniseed oil, thyme oil, geranium oil, lavender oil, menthol as well as synthetic, oil-soluble perfume oils from the group of the aldehydes, esters and polyene compounds.
The quantity ratios of fat-soluble perfume oil and hydroxy-alkylester-oxethylate in the clear, stable, aqueous or aqueous-alcoholic solutions in accordance with the invention can vary within wide limits and depend upon the type of perfume oil, the type of dissolving intermediary, the alcohol content and other accompanying substances which are present in the solution. The hydroxyalkylester-oxethylates can be present in quantities of from 0.1 to 20 percent by weight in the solutions in accordance with the invention, although they will generally be present in quantities of from 0.5 to 5 percent by weight. It will be assumed that the desired quantities of perfume oil will not substantially exceed or fall below the limits of from 0.1 to 1 percent by weight relative to the total solution.
The clear, stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils in accordance with the invention can be produced in a manner known per se by adding water or an alcohol-water mixture in the desired quantity ratio to corresponding concentrates of perfume oil and hydroxyalkylether-oxethylate.
The following Examples are intended to further explain the subject of the invention, but without limiting the invention to these Examples.
The hydroxyalkylether-oxethylates to be used in accordance with the invention were produced in a generally known manner by reacting corresponding epoxyalkanes with ethylene glycol in the presence of acid catalysts such BF3 or complexes thereof, or by means of alkaline catalysts such as sodium methylate. The hydroxyalkylether produced was subsequently ethoxylated in an autoclave in a conventional manner with the desired quantities of ethylene oxide in the presence of alkaline catalysts.
The following experiments were carried out for the purpose of testing the dissolving intermediary properties. A 1% by weight aqueous solution of the perfume oil used was produced in each case. For this purpose, the perfume oil was in the first instance agitated together with the respective dissolving intermediary in a specific quantity ratio, and sufficient water was subsequently added to produce a 1% by weight solution relative to perfume oil. The weight ratio of dissolving intermediary:perfume oil chosen was 7:3 and 8:2 respectively, corresponding approximately to a 2-fold to 4-fold quantity of dissolving intermediary relative to perfume oil.
The following substances acted as dissolving intermediaries:
L 1 a-Cl6Xl8-epoxide + glycol + 11 EO
L 2 a-C16118-epoxide + glycol + 13 EO
L 3 o:-C14,16-epoxide + glycol + 7 EO
L 4 a-Cl4,l6-epoxide + glycol + 9 EO
L 5 a-Cl4,16-epoxide + glycol + 10 EO
L 6 a-Cl4,l6-epoxide + glycol + 11 EO
L 7 i-Cll,14-epoxide + glycol + 5 EO
L 8 i-C1 1114-epoxide + glycol + 8 EO
L 9 i-Cll,14-epoxide + glycol + 10 EO
L 10 i-Cl5,l8-epoxide + glycol + 7 EO
L 11 i-C15118-epoxide + glycol + 9 EO
L 12 i-C1511-epoxide + glycol + 10 EO
L 13 i-Cl5,18-epoxide + glycol + 11 EO
L 14 Castor oil + 40 EO (comparison substance)
10 etheral oils of differing composition and polarity acted as the test substances.
01 Rosemary oil 06 Orange oil
02 Bergamot oil 07 Pine oil
03 Cedar wood oil 08 Peppermint oil
04 Carnation petal oil 09 Patchouli oil
05 Oil of lemons 010 Lavandine oil
The results of the individual aqueous solutions are given in the following Table 1, wherein x = turbid solution, xx = slightly turbid solution and xxx = clear, stable solution.
Furthermore, the Table shows how many different oils a dissolving intermediary is able to dissolve. The larger the number of oils used which a dissolving intermediary can dissolve, the higher is its assessment as a dissolving intermediary in general, since it can be used more universally. Naturally, the results given in the Table can be improved by a higher ratio of dissolving intermediary : perfume oil.
TABLE 1
Dissolving Ratio intermediary DI:oil 01 02 03 04 05 06 07 08 09 010 Number of oils dissolved
L 1 7 :3 xxx xxx xxx xx xxx xxx xxx xxx xxx xx 10 8 : 2 xxx xxx xxx xxx xxx xxx xxx xxx xxx xxx
L 2 7 : 3 xxx xxx xxx xxx xxx xxx x x xxx x 7 8 : 2 xxx xxx xxx xxx xxx xxx xx xx xxx xx
L 3 7 : 3 xxx xxx x xxx xxx xxx xxx x x xxx 9 8 : 2 xxx xxx x xxx xxx xxx xxx xxx xxx xxx
L 4 7 : 3 xx xx xx xxx xx xxx xxx x xx x 9 8 : 2 xxx xxx xxx xxx xxx xxx xxx xxx xxx xx
L 5 7 : 3 xxx xxx xxx xxx xxx x xxx x xxx x 10 8 : 2 xxx xxx xxx xxx xxx xxx xxx xxx xxx xxx
L 6 7 : 3 xxx xx xxx xxx x x xxx x xx x 5 8 : 2 xxx xxx xxx xxx xx x xxx x x x
L 7 7 : 3 x x xxx x xxx xxx x x x x 5 8 : 2 xxx xxx xxx x xxx xxx x x x x TABLE I (Continued)
Dissolving Ratio intermediary DI:oil 01 02 03 04 05 06 07 08 09 010 Number of oils dissolved
L 8 7 : 3 x x x x x x x x x x 5 8 : 2 x xxx x xxx x x xxx xxx x xxx
L 9 7 3 x x x x x x xxx x x x 2 8 : 2 x x x xxx x x xxx x x x
L 10 7 3 x xxx xxx x xxx xxx x x x x 6 8 : 2 xxx xxx xxx x xxx xxx x x xxx x
L 11 7 : 3 xxx xxx xxx x xx xx x xxx x xxx 8 8 : 2 xxx xxx xxx xx xxx xx xxx xxx xxx xxx
L 12 7 : 3 xxx xxx xxx x xx xxx xxx xxx xxx x 10 8 : 2 xxx xxx xxx xxx xxx xxx xxx xxx xxx xxx
L 13 7 : 3 xxx x xx xxx xxx xxx xxx xxx xxx xx 9 8 : 2 xxx xxx xx xxx xxx xxx xxx xxx xxx xxx
L 14 7 : 3 x x x x x x x x x x 0 8 : 2 xx xx xx xx xx xx x xx xx xx In order to produce aqueous-alcoholic solutions having the same quantity of fat-soluble perfume oil, the quantities of dissolving intermediary required naturally decrease as the alcohol content increases, in order to obtain clear solutions.
Claims (7)
1. Clear, stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils, having a content of hydroxyalkyl-ether-oxethylates of the general formula
in which R1 and/or R2 represent an alkyl group having 1 to 24 carbon atoms or hydrogen, or
R3 and/or R4 represent an alkyl group having 2 to 22 carbon atoms or hydrogen, with the proviso that the total of the carbon atoms of R1 + R2 or R3 + R4 lies in the range of from 2 to 26, and x and y can represent integers of from 1 to 16, with the proviso that the total of the integers x and y has values of from 2 to 18.
2. Clear, stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils as claimed in claim 1 wherein, in the general formula, R1 and/or R2-represent an alkyl group having 12 to 18 carbon atoms, or R3 and/or R4 represent an alkyl group having 12 to 18 carbon atoms, with the proviso that the total of the carbon atoms of R1 + R2 or R3 + R4 lies in the range of from 6 to 20, and x and y can represent integers of from 8 to 14, with the proviso that the total of the integers x + y has values of from 8 to 14.
3. Clear, stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils as claimed in claim 1 or 2, having a content of hydroxyalkylether-oxethylates which are derived from unbranched and 2-alkyl branched end position C14-C16- or Cl6-Cl8- epoxy alkanes and inner position Ct,-C,8-epoxy alkanes and have 8 to 14 ethylene oxide groups added thereto.
4. Clear, stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils as claimed in claim 1, 2 or 3 having a content of compounds of the general formula which are the products of reaction from a-C14116-epoxide + glycol + 9 EO, a-C14/16-epoxide + glycol + 10 EO, a-C14116-epoxide + glycol + 11 EO, a-C16118-epoxide + glycol + 8.7 EO, a-C16118-epoxide + glycol + 11 EO, a-C16118-epoxide + glycol + 13 EO, i-C15,,8-epoxide + glycol + 9 EO, i-Cls,l8-epoxide + glycol + 10 EO or i-C15118-epoxide + glycol + 11 EO.
5. Clear, stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils as claimed in any one of claims 1 to 4, having a content of hydroxyalkylether-oxethylates of the aforementioned formula in a quantity of from 0.1 to 20 percent by weight, relative to the total solution.
6. Clear, stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils as claimed in claim 5 in which the quantity is from 0.5 to 5 percent by weight.
7. Clear, stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils as claimed in claim 1 and substantially as hereinbefore described with reference to the
Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772731218 DE2731218A1 (en) | 1977-07-11 | 1977-07-11 | STABLE AQUATIC OR Aqueous-ALCOHOLIC SOLUTIONS OF FAT-SOLUBLE PERFUME OILS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1601983A true GB1601983A (en) | 1981-11-04 |
Family
ID=6013629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22711/78A Expired GB1601983A (en) | 1977-07-11 | 1978-05-25 | Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5420146A (en) |
| CH (1) | CH636267A5 (en) |
| DE (1) | DE2731218A1 (en) |
| FR (1) | FR2397188A1 (en) |
| GB (1) | GB1601983A (en) |
| IT (1) | IT1097480B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006087569A2 (en) * | 2005-02-17 | 2006-08-24 | Bio-Life Medicare Limited | Antimicrobial composition comprising an extract of tarchonanthus camphoratus |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2913467A1 (en) * | 1979-04-04 | 1980-10-16 | Henkel Kgaa | STABLE AQUEOUS OR AQUEOUS ALCOHOLIC SOLUTIONS OF FAT-SOLUBLE PERFUME OILS |
| EP0571677A1 (en) * | 1992-05-29 | 1993-12-01 | Unilever Plc | Aqueous parfume oil microemulsions |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB547536A (en) * | 1941-04-25 | 1942-09-01 | Stafford Allen & Sons Ltd | Improvements in the manufacture of fixatives for perfumery |
| US2538576A (en) * | 1947-04-23 | 1951-01-16 | Gus H Mavrakis | Fishing creel or basket |
| DE865510C (en) * | 1948-06-30 | 1953-02-02 | Basf Ag | Process for the production of mixtures of substances which are insoluble or only slightly soluble in water, which can be diluted with water without excretions |
| FR1159324A (en) * | 1956-10-12 | 1958-06-26 | Low alcohol cologne | |
| US3119848A (en) * | 1962-01-11 | 1964-01-28 | Arthur N Wrigley | Oxyethylated diols, nitriles and soaps |
| DE1910765U (en) | 1964-11-07 | 1965-02-25 | Erwin Kroemker | GEAR AND GUIDE FITTINGS FOR COVERING TRIMS OF GLAZED SURFACES, IN PARTICULAR OF GREENHOUSES. |
| FR2003231A1 (en) * | 1968-03-05 | 1969-11-07 | Monsanto Co |
-
1977
- 1977-07-11 DE DE19772731218 patent/DE2731218A1/en not_active Withdrawn
-
1978
- 1978-05-25 GB GB22711/78A patent/GB1601983A/en not_active Expired
- 1978-07-05 IT IT25341/78A patent/IT1097480B/en active
- 1978-07-10 JP JP8311578A patent/JPS5420146A/en active Pending
- 1978-07-10 CH CH747878A patent/CH636267A5/en not_active IP Right Cessation
- 1978-07-11 FR FR7820643A patent/FR2397188A1/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006087569A2 (en) * | 2005-02-17 | 2006-08-24 | Bio-Life Medicare Limited | Antimicrobial composition comprising an extract of tarchonanthus camphoratus |
| WO2006087569A3 (en) * | 2005-02-17 | 2006-10-26 | Bio Life Medicare Ltd | Antimicrobial composition comprising an extract of tarchonanthus camphoratus |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2397188B1 (en) | 1981-07-31 |
| IT1097480B (en) | 1985-08-31 |
| JPS5420146A (en) | 1979-02-15 |
| CH636267A5 (en) | 1983-05-31 |
| DE2731218A1 (en) | 1979-02-01 |
| FR2397188A1 (en) | 1979-02-09 |
| IT7825341A0 (en) | 1978-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2866895B1 (en) | Surfactant solutions containing n-methyl-n-oleylglucamines and n-methyl-n-c12-c14-acylglucamines | |
| EP0716680B1 (en) | Use of aqueous detergent mixtures | |
| EP2825151B1 (en) | Composition | |
| TW519535B (en) | Higher secondary alcohol alkoxylate compound composition, method for production thereof, and detergent and emulsifier using the composition | |
| US4184985A (en) | Stable, aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils containing hydroxyalkyl ether-ethoxylates | |
| EP0201016A2 (en) | Builder-free liquid detergents with softening properties | |
| JP2011136995A (en) | Fragrance microemulsion composition | |
| EP0333143B1 (en) | Medicinal soaps | |
| EP0018482A1 (en) | Biodegradable and low foaming surfactants, process for their preparation and their use in detergents | |
| KR20070095321A (en) | Personal care compositions | |
| US4299737A (en) | Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils | |
| US4170655A (en) | Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils or drugs containing hydroxyalkyl ester- or N-(hydroxyalkyl) amide-ethoxylates | |
| GB1601983A (en) | Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils | |
| EP1441024B1 (en) | Use of solubilizers for aqueous detergent compositions containing a perfume | |
| EP0703973B1 (en) | Aqueous bleaching agents | |
| CH668266A5 (en) | SURFACTANT MIXTURES. | |
| US4186207A (en) | Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils or drugs containing N-(hydroxyalkyl)amide-ethoxylates | |
| EP0022460A1 (en) | Aliphatic ethers of hydroxymethylcyclododecane and their utilization in the preparation of odorant compositions | |
| US3877955A (en) | Cosmetic compositions | |
| US2290908A (en) | Shampoo | |
| DE3432219A1 (en) | Solubilisers for oil-soluble perfume oils | |
| EP2480646B1 (en) | Unperfumed cleaning agent | |
| JPH09183995A (en) | Perfume composition | |
| DE10046432A1 (en) | New terpene alcohol ethers, used as oil component in skin care formulation, and adducts used in skin cleanser or shampoo, are reaction products of terpene alcohol and long-chain epoxide compound | |
| DE3125109A1 (en) | DIACETYLENDIAL CHARCOALS, THEIR ETHOXYLATES AND THE USE OF THESE COMPOUNDS AS A SURFACTANT |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |